Vacation rentals in Chesapeake

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Top-rated vacation rentals in Chesapeake

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Guest favorite
The exterior of the house is highlighted by a charming gabled roof and white clapboard siding. A stone chimney rises from the roof, and the entrance features a set of steps leading to a welcoming front door framed by large windows on either side, surrounded by lush green grass and trees.
Home in South Hills
4.89 out of 5 average rating, 315 reviews

Historic Farmhouse by Nature Preserve

We welcome you to The Little House, sensitively restored and superbly furnished. Enjoy entire house and its 2.7 acres, adjacent to 52 acres of walking trails, while still in the heart of town. Ideal for nature-seekers and business travelers alike. Calm, quiet environs in which to read a book— or write one. One loft bedroom with one full bed + one (30" x 70") daybed. One pull-out loveseat in sitting room; 2 stored iBeds. Note all bedding details under Space. Re: pets: one dog allowed. No cats.

Top guest favorite
An open living space features a comfortable couch with yellow accent pillows and a coffee table. A fully equipped kitchen is visible, with stainless steel appliances and modern cabinetry. A full-size bed is showcased against a wooden accent wall, with soft bedding inviting restful sleep.
Place to stay in Cross Lanes
4.96 out of 5 average rating, 208 reviews

Spectacular Storage Unit! 😉 Just Off I-64

Have you ever wondered what it would be like to stay overnight in a mini-storage? Probably not, lol! But if you've ever watched HGTV, you'll see that people across the country are creating short-term rentals out of all kinds of crazy things, from shipping containers and barns, to old warehouses. Well, in Cross Lanes WV, we took our cues from those folks on TV and created a short-term rental out of a storage unit! Conveniently located, just off I64, and only 1 mile to the Mardi Gras Casino.

Guest favorite
A welcoming front entrance features a decorative sign that reads 'Welcome Americana Cottage' against a backdrop of a red door. A festive red, white, and blue fan decoration is displayed beside the door, adding a touch of American pride, complemented by a soft glow from an exterior light fixture.
Home in West Side
4.96 out of 5 average rating, 139 reviews

Americana Cottage at Luna Park Historic District

You will be close to everything when you stay at this centrally-located home in Charleston’s Luna Park Historic District. Americana Cottage was built in 1920 at the cornerstone of the once renowned Luna Amusement Park. It boasts antique furnishings, cozy decor and a 2 level deck with fire pit. 2 blocks from the river. Within 10 minutes of all major hospitals, shopping, dining and entertainment, Americana Cottage is perfect for families, travel nurses and business travelers. A very unique stay!

Guest favorite
The living room features a comfortable reclining couch and a bright red armchair, complemented by large windows dressed with yellow curtains. A colorful area rug covers the hardwood floor, while a small TV is set on a side table, providing a cozy space with natural light.
Home in Dunbar
4.99 out of 5 average rating, 119 reviews

River View Cottage

Keep it simple at this peaceful & centrally-located river cottage in Dunbar, WV. Enjoy the river view from this 2 bed/1 bath home updated and fully stocked for your stay. Convenient to the interstate, restaurants, shopping, hospitals & 1.5 miles from the Shawnee Sports Complex. We are 10-15 minutes from downtown Charleston, Mardi Gras Casino & Resort, Clay Center, Charleston Coliseum & Convention Center. We offer keyless entry and a home security system. Off-street parking. No pets allowed.

Guest favorite
A rustic cabin exterior is framed by trees, featuring a wooden porch with steps leading to a front door. Firewood is stacked neatly beside the entrance, while the surrounding area showcases a grassy patch and natural ground cover.
Cabin in Clendenin
4.92 out of 5 average rating, 114 reviews

RealTree Camo Cabin 3

This cabin is rustic and small but super cozy! It's comfortable with a queen size bed, a wood burning stove, air conditioning, fridge freezer, coffee, creamer & sugar provided, a smart tv & more. The creek runs in front of it and is literally up against a mountain, surround by mountains. This cabin is located right beside the shower house. There are beautiful hiking trails, a coal mine is a short hike away and a secret wilderness chapel. Enjoy some simple time up & away from town life.

Guest favorite
A serene pond is surrounded by lush landscaping and illuminated with twinkling lights. The soothing water features a gentle fountain in the center. An old car rests on the shore, adding a unique vintage touch to the peaceful outdoor atmosphere.
Guest suite in Charleston
4.91 out of 5 average rating, 135 reviews

Retreat in the mountains with new hot tub & deck.

Located in Charleston,WV near CAMC Memorial Hospital. 10 minutes away from Yeagar Airport.This fully furnished basement has recently been remodeled which provides a quiet and clean space to relax or work. King size bed and queen size pull out sofa. Air mattresses available. Two full baths. Brand new hot tub. Jacuzzi tub. You can relax and unwind on the deck while over looking the pond and waterfall. At night you can take a leisurely walk around the pond under the lights.Free Wi-Fi.

Guest favorite
Guesthouse in Elkview
4.94 out of 5 average rating, 303 reviews

River Retreat

In need of a long-term stay offering peace, quiet, and convenience?This beautiful, open garage studio has just what you need on the Elk River. Property has multiple private entries & off street parking in a residential area. Minutes from the airport; Interstates 64, 77, and 79; hospitals; Coonskin Park; & Elk River Trail. Property has modern amenities and is sanitized for your health. Come get away without being too far away from the convenience of the city. Long-term guests only.

Top guest favorite
A modern front door is opened wide, inviting guests into the home. A welcome mat featuring the phrase 'WELCOME HOME' is visible on the doorstep. Light-colored flooring can be seen inside, along with a glimpse of decor and furnishings.
Home in Charleston
5 out of 5 average rating, 135 reviews

The 505 on Margaret

Welcome to our custom-built brand-new house in the heart of Charleston West Virginia. This house was completed June 2024 and has been furnished, stocked, and designed with the most modern and updated materials. We have specifically designed this house for nightly, weekly or month-long stays. Located 2 blocks from the Charleston Coliseum and a short walk to the lively capitol street. Check out our other house next door to this one, The 314 on Joseph. Children and pets are welcome.

Guest favorite
A comfortable living area features a mix of seating options, including bright blue chairs and a cozy hanging chair. A television is mounted on a shelf adorned with bear-themed decorations. Natural light pours in through large windows, enhancing the warm ambiance of the space.
Guesthouse in Charleston
4.93 out of 5 average rating, 310 reviews

The BearBnB - Pet friendly, 10 mins to downtown

Take it easy at this almost heaven hideaway. This adorable, Bear themed loft gives you the country setting you’re looking for and the convenience you need. Located just 10 minutes from downtown Charleston and Yeager Airport. Enjoy the peace and quiet of nature or hop downtown for an array of shopping and eatery selections. Tour the West Virginia State Capitol topped with its gorgeous gold dome or dive into WV’s many adventures. Business or pleasure, you’ll love the Bear BNB

Guest favorite
The kitchen features white cabinetry and appliances, including a refrigerator, stove, and oven. A small round table with two metal chairs is positioned near a window, dressed in light curtains. A decorative bowl of fruit adds a pop of color on the table.
Apartment in Kanawha City
4.96 out of 5 average rating, 147 reviews

Enjoy our Cozy Garage Apartment

You will love staying in this one bedroom garage apartment, located in the neighborhood of Kanawha City, in the south east section of Charleston , West Virginia. Situated on the Kanawha River, we are minutes from grocery stores and restaurants. We are less than 10 miles from downtown Charleston which has a lot to offer in cultural experiences and locally owned restaurants and businesses. Enjoy the neighborhood feel and enjoy the view of the mountains and the beautiful river.

Guest favorite
A serene river view is captured, featuring the tranquil water flowing beside a grassy area. Lush green trees line the bank, complemented by a mountainous backdrop, creating a peaceful natural setting.
Home in Belle
4.92 out of 5 average rating, 159 reviews

River Retreat,LLC/4.5 m to Charleston/River access

Unwind in the serenity of this beautiful home, situated in the heart of the Appalachian Mountains, where you can gaze at the breathtaking Kanawha River and mountainous backdrop from the comfort of a covered patio. Includes access to the river for fishing or kayaking (gear not included). Minutes away from historic Charleston, offering a balance of access to city attractions with a scenic place to rest after adventuring. Close to Interstates 64, 77, and 79. No cleaning fee.

Top guest favorite
A modern living area features a gray sectional sofa adorned with yellow decorative pillows. A white coffee table is positioned in front, and a built-in shelving unit displays colorful decor items. A dining area is visible in the background, showcasing a round table and chairs.
Condo in Charleston
5 out of 5 average rating, 195 reviews

Trier Loft at Renaissance Tower

Trier Loft is a luxury downtown condominium located on picturesque Capital Street in Charleston, WEST VIRGINIA. It is in a 100+ year old building that was originally the KB&T Building. There are spectacular views of Charleston and its surrounding hills from its 5th floor vantage point. It is within easy walking distance to Charleston's most popular restaurants, bars, theaters, specialty shops, and concert venues.

Popular amenities for Chesapeake vacation rentals